| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2008-10-29 06:24:48 -0600 |
| Update Date |
2013-03-26 16:15:27 -0600 |
| HMDB ID |
HMDB11133 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
DHAP(18:0) |
| Description |
DHAP(18:0) is the octadecanoyl derivative of dihydroxyacetone phosphate. It is also known as an alkyl-DHAP. This compound is formed by octadecanoic acid reacting with DHAP. Alkyl-DHAPs are intermediates in the synthesis of ether phospholipids. The initial steps of ether phospholipid biosynthesis take place in peroxisomes. Alkyl-dihydroxyacetonephosphate synthase is the peroxisomal enzyme that actually introduces the ether linkage. Levels of Alkyl-DHAP have been found to be strongly reduced in human fibroblasts derived from Zellweger syndrome and rhizomelic chondrodysplasia punctata patients. Four other enzymes are known to be involved in the metabolism of acyl-DHAP and alkyl-DHAP. These include: acyl-DHAP/alkyl-DHAP oxidoreductase, DHAP acyltransferase, alkyl-DHAP phosphohydrolase, and a dinitrofluorobenzene-insensitive acyl-DHAP acylhydrolase. Dihydroxyacetone phosphate (DHAP) is a biochemical compound primarily involved in the glycolysis metabolic pathway. DHAP is also the product of the dehydrogenation of L-glycerol-3-phosphate which is part of the entry of glycerol (sourced from triglycerides) into the glycolytic pathway. Conversely, reduction of glycolysis-derived DHAP to L-glycerol-3-phosphate provides adipose cells with the activated glycerol backbone they require to synthesize new triglycerides. Both reactions are catalyzed by the enzyme glycerol 3-phosphate dehydrogenase with NAD+/NADH as cofactor. DHAP may be referred to as glycerone phosphate in older texts. 1-Octadecyl-glycerone-3-phosphate is an intermediate in Ether lipid metabolism. DHAP(18:0) or 1-Octadecanoyl-glycerone-3-phosphate is the precursor to 1-Octadecyl-glycerone-3-phosphate DHAP(18:0e) which is generated via alkylglycerone phosphate synthase (EC: 2.5.1.26). Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. Ether lipids are called plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) if these are glycerol-containing phospholipids with an unsaturated O-(1-alkenyl) (vinyl ether) group at the first position on the glycerol chain. Plasmalogens as well as some 1-O-alkyl lipids are ubiquitous and sometimes major parts of the cell membranes in mammals and anaerobic bacteria. In archaea, ether lipids are the major polar lipids in the cell envelope and their abundance is one of the major characteristics that separate this group of prokaryotes from the bacteria. In these cells, diphytanylglycerolipids or bipolar macrocyclic tetraethers can form covalently linked 'bilayers'. (Wikipedia) |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 1-Octadecanoyl DHAP
- 1-Octadecanoyl Dihydroxyacetone phosphate
- 1-Octadecanoyl-glycerone-3-phosphate
- 1-Stearoylglycerone 3-phosphate
|
| Chemical Formula |
C21H41O7P |
| Average Molecular Weight |
436.5198 |
| Monoisotopic Molecular Weight |
436.258990178 |
| IUPAC Name |
[3-(octadecanoyloxy)-2-oxopropoxy]phosphonic acid |
| Traditional IUPAC Name |
3-(octadecanoyloxy)-2-oxopropoxyphosphonic acid |
| CAS Registry Number |
Not Available |
| SMILES |
CCCCCCCCCCCCCCCCCC(=O)OCC(=O)COP(O)(O)=O |
| InChI Identifier |
InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h2-19H2,1H3,(H2,24,25,26) |
| InChI Key |
GTPATKZCXDKGQS-UHFFFAOYSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Fatty Acid Esters |
| Sub Class |
N/A |
| Other Descriptors |
- 1-acylglycerone 3-phosphate(ChEBI)
- Aliphatic Acyclic Compounds
|
| Substituents |
- Alpha Ketoaldehyde
- Carboxylic Acid Ester
- Ketone
- Organic Hypophosphite
- Organic Phosphite
- Phosphoric Acid Ester
|
| Direct Parent |
Fatty Acid Esters |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
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| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
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| Biological Properties |
|---|
| Cellular Locations |
|
| Biofluid Locations |
Not Available
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| Tissue Location |
Not Available
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| Pathways |
| Name |
SMPDB Link |
KEGG Link |
| Plasmalogen Synthesis |
SMP00479
|
Not Available
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| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
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|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB027912 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
389126  |
| KEGG Compound ID |
C03805 |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB11133 |
| Metagene Link |
HMDB11133 |
| METLIN ID |
Not Available |
| PubChem Compound |
440127 |
| PDB ID |
Not Available |
| ChEBI ID |
36476 |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
Not Available |
